Somebody has to notice when a job has gone past its date. If that somebody is you, two things happen. It takes a chunk of your morning, and you become the person who nags – which quietly changes how your team talks to you about everything else, including the things you most need to hear.
So the question is worth answering precisely rather than by instinct: how often, and for how long?
The answer: three times, then stop
Three attempts, at widening intervals, privately, inside working hours. Then stop chasing and have a different conversation instead.
The number three is not sacred – two works, four is defensible. What matters enormously is that there is a number, decided in advance. An unbounded chase is the failure mode, and it is the most common one.
Why the limit is the important part
Consider what somebody learns from being reminded a seventh time about the same job.
They learn that the reminder is not a signal, it is weather. It arrives whatever they do. It carries no information, because attempt seven looks exactly like attempt two. So they stop reading it – and because it is indistinguishable from every other reminder, they start ignoring the ones that matter as well.
A chase that stops after three attempts is different in kind. Each one means something, because there are only three. And the fact that it stops is what makes the escalation meaningful: when the reminders end and the owner appears, everybody understands that something changed.
The same logic explains why automated chasing so often fails. A tool that reminds indefinitely gets muted within a week – and a muted tool is worse than no tool, because the owner still thinks it is working.
The four other rules
Privately, always. Nobody’s late work belongs in a group chat. Public chasing gets a faster response once and costs you candour permanently, because everybody now knows that admitting a problem is a public event.
Only inside working hours. A reminder at nine at night is not diligence, it is a message that says your evening is available to me. People do not forget it, and they do not respond to it well.
Only about their own work. Obvious, and routinely broken by group-level reminders that make everybody feel chased so that one person will act.
Never chase blocked work. This is the rule most often broken and the most damaging. If somebody has told you they are waiting on a supplier, chasing them teaches them that reporting a blocker earns them a nagging and changes nothing. Next time they will not tell you. See blocked is not the same as late.
What happens after the third attempt
Not a fourth reminder. A different conversation – and it is a short one, with three possible answers.
- They are blocked and had not said. Now you know, and you can unstick it. This is the most common outcome and it is a good one.
- They have too much on. Also useful. You have found a load problem, which is a you problem rather than a them problem.
- They are not doing it and there is no reason. Rare, and this is the conversation that actually needed having. Three automated reminders were never going to produce it.
In all three cases the reminders had done their job, which was to establish that a conversation was needed – not to substitute for one.
Hand it to software if you can
Chasing is an unusually good candidate for automation, because it is repetitive, unrewarding, and damaging to whoever does it. Software has no feelings about sending the same reminder for the third time, and – this matters more than it sounds – people do not resent software the way they resent a manager.
The constraints are the rules above rather than anything clever. In Bosun they are the defaults: three attempts, widening intervals, private messages, inside your working hours, blocked work exempt, then it stops and tells you. All of it adjustable, and the limits are on by default rather than being a setting you have to discover. See automatic follow-up.
One warning that applies whatever you use: automating the chasing does not automate the replying. If updates still disappear into nothing, they will stop arriving however politely the reminder was worded.